Cesium carbonate → HCID 86668515, compound

HRID 2047255Notes

Reaction equation

Br[C:2]1[C:3]([C:23]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:30])=[N:4][O:5][C:6]=1[C:7]1[CH:8]=[N:9][N:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11]=1[C:12]([F:15])([F:14])[F:13].[O:31]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[Cl:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([F:29])[C:23]=1[C:3]1[C:2]([C:33]2[CH:34]=[CH:35][O:31][CH:32]=2)=[C:6]([C:7]2[CH:8]=[N:9][N:10]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:11]=2[C:12]([F:15])([F:14])[F:13])[O:5][N:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The tube was charged with 4-bromo-3-(2-chloro-6-fluorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole (30 mg, 0.06 mmol), tetrakis(triphenylphosphine)palladium(0) (0.010 g), 1.5 mL 1,2-Dimethoxyethane and was purged with argon. Then furan-3-ylboronic acid (0.012 g, 0.1 mmol) and an aqueous solution of cesium carbonate (0.05 g in 0.2 mL) were added. The reaction mixture was heated under microwave irradiation to 100° C. for 2 h. The solvent was evaporated and the product was isolated by column chromatography (hexane:ethyl acetate 25: I) to obtain 5 mg (17%) of a yellowish solid of example I-13. As a major side reaction, hydrodebromination was observed.

Workup

customwas purged with argon
customThe solvent was evaporated
customthe product was isolated by column chromatography (hexane:ethyl acetate 25: I)

Sources & evidence

ORD record: ord-505f2f505f64492c9a5345d86828e4e9
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592456B2

Reaction notes

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